This application is a 371 of PCT/EP98/02014, filed Apr. 7, 1998.
The present invention relates to aromatic amides, their preparation process and their use as pesticides.
A subject of the invention is the compounds of formula (I): 
in which:
a, b, c and d, identical to or different from one another, represent a hydrogen atom, a halogen atom, an alkyl, alkenyl or alkynyl, O-alkyl, O-alkenyl or O-alkynyl, S-alkyl, S-alkenyl or S-alkynyl radical containing up to 8 carbon atoms, optionally substituted by one or more halogen atoms, a Cxe2x89xa1N, NO2 or NH2 radical, the substituents a, b, c and d being able to form between themselves rings, preferably one, which either contain or do not contain one or more, preferably one or two, hetero atoms, preferably from the group consisting of S, O and N, and which are substituted, or unsubstituted.
Y and W, identical to or different from one another,
represent both a 
xe2x80x83radical or both a 
xe2x80x83radical in which e, f and exe2x80x2, identical or different, represent a hydrogen atom, a halogen atom, a free, etherified or esterified hydroxyl radical, or an alkyl radical containing up to 8 carbon atoms optionally substituted by one or more halogen atoms;
X represents a 
xe2x80x83radical or a 
xe2x80x83radical in which g, h and gxe2x80x2, identical or different, represent a hydrogen atom, a halogen atom, a free, etherified or esterified hydroxyl radical, or an alkyl radical containing up to 8 carbon atoms optionally substituted by one or more halogen atoms, or X represents a Cxe2x95x90O radical, an oxygen atom or a nitrogen atom, or X forms with the carbon in position 2 belonging to radical q an epoxy bridge, a cyclic hydrocarbonated radical optionally substituted by one or more halogen atoms;
q represents a Cxe2x95x90 radical or a CD radical, in which D represents a hydrogen atom, a halogen atom or an alkyl or alkoxy radical containing up to 8 carbon atoms optionally substituted by one or more halogen atoms, or D forms with the carbon atom which carries it and one of the carbon atoms adjacent to it a carbon-carbon double bond, an epoxy radical, a cyclic hydrocarbonated radical, optionally substituted by one or more halogen atoms;
n represents an integer varying from 0 to 8;
Z represents a 
xe2x80x83radical in which I and k, identical or different, represent a hydrogen atom, a halogen atom, a Cxe2x89xa1N radical, a free, etherified or esterified hydroxyl radical, an SRxe2x80x2 radical, wherein Rxe2x80x2 is an organic rest containing up to 8 carbon atoms, preferably S-alkyl, or an alkyl radical containing up to 8 carbon atoms optionally substituted by one or more halogen atoms, or Z represents an oxygen, sulfur, nitrogen atom, a Cxe2x95x90O or Cxe2x95x90S radical, it being understood that if n is greater than 1, Z can take different values,
R represents an oxygen or sulfur atom;
R1 and R2, identical to or different from one another, represent a hydrogen atom, a linear, branched or cyclic, saturated or unsaturated, optionally substituted alkyl, CO-alkyl, CONH-alkyl or CO2 alkyl radical contaning up to 8 carbon atoms, optionally interrupted by one or more preferably non-adjacent heteroatoms, preferably from the group consisting of N, O, S, or an optionally substituted aryl or heteroaryl radical,
the xe2x80x94Cxe2x80x94(Z)n chain is fixed in position 3 or 4 of the benzamide, the dotted lines representing one or more optional double bonds,
in all their possible isomeric forms as well as their mixtures.
By compound of formula (I) are designated all the geometric isomers and stereo-isomers taken individually or in a mixture.
In the definition of substituents:
alkyl preferably represents a methyl, ethyl, propyl, isopropyl, butyl, isobutyl,
n-pentyl, isopentyl, cyclopropyl, cyclobutyl or cyclopentyl radical,
alkenyl preferably represents a vinyl, 1-propenyl, 2-methyl 2-propenyl or isopropenyl radical,
alkynyl preferably represents an ethynyl, 1-propynyl, 2-propynyl or pent-2-ene-4-enyl radical,
halogen preferably represents a fluorine, chlorine, bromine or iodine atom,
aryl preferably represents a carbocyclic aromatic group containing 4 to 10 carbon atoms, particularly preferably a phenyl, naphthyl, dihydronaphthyl, tetrahydronaphthyl, indanyl or indenyl radical,
a heterocyclic radical is preferably a heteroaryl radical or a saturated or unsaturated 3 to 8 membered ring comprising one, two three or four heteroatoms from the group consisting of N, O and S.
heteroaryl is preferably a 3 to 7 membered aromatic ring comprising one, two, three or four heteroatoms from the group consisting of N, O and S, particularly preferred thienyl, furyl, pyrrolyl, imidazolyl, pyrazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isothiazolyl, isoxazolyl, oxazolyl, thiazolyl, oxadiazolyl and tetrazinyl
Particularly preferred heterocyclic radicals are a thienyl, furyl, pyrannyl, pyrrolyl, 2H-pyrrolyl, imidazolyl, pyrazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isothiazolyl, isoxazolyl, furazanyl, thiazolyl, oxazolyl, pyrrolidinyl, pyrrolinyl, imidazolidinyl, pyrazolinyl, piperidyl, piperazinyl, morpholinyl, izapinyl, thiazinyl, tetrazinyl, oxathiolanyl or thiadiazinyl radical.
When the aryl or heterocyclic radical is substituted, it is preferably substituted by one or more substitutents chosen in particular from halogen atoms, alkyl or alkoxy radicals containing up to 8 carbon atoms, or methylenedioxy, difluoromethylenedioxy, tetrafluoro ethylenedioxy, cyano, nitro, cyanato, thiocyanato, pentafluorothio or fluorosulfonyl groups.
Etherified or esterified preferably means etherified with a linear or branched C1-C8-alkyl group or esterified with a (C1-C8)-carboxylic acid.
If any of the substituents a-d form a ring it is preferably a 4 to 8 membered ring which is preferably monounsaturated (due to fusion with the naphthyl group) and is carbocyclic or contains preferably one or two heteroatoms from the group consisting of N, O and S.
If Z is O, N, or CO, CS and n is greater then 1 it is preferred that heteroatoms are not adjacent to each other and CO, CS are not adjacent to each other.
It goes without saying that x, q and Z have to be chosen in a way that a tetravalent carbon at q results.
Particularly preferred are compounds of formula (I) in which Y represents a xe2x80x94CH2xe2x80x94 radical, those in which Y and W represent a CH radical and together form a double bond in position 3(4), those in which W represents a CH2 radical, those in which q and X represent a CHxe2x95x90 radical and together form a double bond, those in which q represents a CH or Cxe2x95x90 radical, those in which X represents a CH, a CH2, a CHOH or a CO radical, those in which Z represents a CH2 a CHF, a CHOH or a COOCH3 radical, those in which n represents the number 1, those in which R represents an oxygen atom, those in which R1 represents a hydrogen atom, those in which R2 represents an alkyl radical containing up to 8 carbon atoms or a phenyl radical optionally substituted by one or more halogen atoms and/or one or more linear or branched alkyl radicals containing up to 8 carbon atoms in particular in which R2 represents an alkyl radical containing up to 6 carbon atoms and in particular an isobutyl radical or a 2-methylphenyl radical, those in which at least one of substituents a, b, c and d represents a halogen atom, (C1-C8) alkyl or (C1-C8) alkoxy for example those in which two of the substituents a, b, c and d represent a chlorine or bromine atom, the compounds of formula (I) in which two of the substituents a, b, c and d represent a hydrogen atom.
In particular a subject of the invention is the compounds the preparation of which is given hereafter in the experimental part and quite particularly the compounds of Examples A, B, C, D, E, F, G, H, I, J, K, L and M.
The compounds of formula (I) can be used to combat harmful organisms such as arthropods, for example insects and acaridae, and helminths, for example nematodes, or molluscs, for example slugs. Therefore a subject of the present invention is a process for combating arthropods and/or helminths and/or molluscs, which comprises the administration to the arthropods and/or helminths and/or molluscs, or to their environment, of a quantity of a compound of formula (I) which is sufficient to destroy the harmful organism. Also a subject of the present invention is a process for combating and/or eradicating infestations by arthropods and/or helminths and/or molluscs of animals (including humans) and/or of plants (including trees) and/or stored products, which comprises the administration to the animal or to the locality of an effective quantity of a compound of formula (I). A subject of the invention is also the compounds of formula (I) to be used in human and veterinary medicine, in public health and/or in agriculture for combating harmful arthropods and/or helminths.
The compounds of formula (I) are particularly valuable in the protection of standing crops, forage crops, crops in plantations, in greenhouses, in orchards and in vineyards, of ornamental plants and trees in plantations and forests, for example cereals (such as corn, wheat, rice, sorghum), cotton, tobacco, vegetables and salad vegetables (such as beans, cabbages, cucurbitaceae, lettuces, onions, tomatoes and peppers), food crops (such as potatoes, sugar beet, peanuts, soya, oilseed rape), sugar cane, meadows and forage (such as corn, sorghum, alfalfa), plantations (such as those producing tea, coffee, cocoa, banana, palm oil, coconut, rubber, spices), orchards and tree plantations (such as those producing stone fruits and pome fruit, citrus fruits, kiwis, avocados, mangoes, olives and walnuts), vines, ornamental plants, flowers and bushes in greenhouses and in gardens and parks, forest trees (both deciduous and evergreen) in forests, plantations and nurseries. They are also valuable in the protection of timber (standing, felled, processed, stored or in buildings) against attack from wood wasps (for example Urocerus) or coleopterous insects (for example scolytidae, platypodidae, lyctidae, bostrichidae, cerambycidae, anobiidae) and termites.
They can be used in the protection of stored products, such as grains, fruits, nuts, spices and tobacco, whether whole, ground or converted into products, against attack from mites, coleopterous insects and weevils. Stored animal products such as skins, furs, wool and feathers, in natural or processed form (for example rugs or textile materials) can also be protected against attack from mites and coleopterous insects; similarly meat and fish can be protected against attack from coleopterous insects and flies.
The compounds of general formula (I) are particularly useful for combating arthropods, helminths or molluscs, which are harmful to man and domestic animals, or spread or are carriers of diseases affecting the latter, for example those which have been described above, and more particularly for combating ticks, mites, lice, fleas, midges and flies which cause bites and are harmful.
The invention also relates to the use of the compounds of formula (I) as defined previously, as pesticides in particular as insecticides, aracides and nematicides in the protection of crops in particular rice and cotton crops, or for the treatment of premises for storing said crops and in particular as insecticides and aracides in domestic or public premises.
The compounds of formula (I) can be used to these ends by the application of the compounds as they are, or in a diluted form, in a known manner, in the form of dips, sprays, mists, lacquers, foams, powders, dusting products, aqueous suspensions, pastes, gels, shampoos, ointments, combustible solids, spray pads, combustible coils, baits, food additives, wettable powders, granules, aerosols, emulsifiable concentrates, oily suspensions, oily solutions, pressurized sprays, impregnated articles, lotions or other standard compositions well known to a person skilled in the art. Concentrates for dips are not used as they are, but diluted with water, and the animals are immersed in a dipping bath containing the dipping product. Sprays can be applied by hand, or by means of a spray lance or frame. The animal, the ground, the plant or the surface can be saturated with the spray using a high volume application, or coated superficially by spraying with a light or very low-volume application. Aqueous suspensions can be applied to the animal in the same manner as sprays or dips. Dusting products must be distributed via a powder applicator or, in the case of animals, be incorporated in perforated bags fixed to trees or poles. Pastes, shampoos and ointments can be applied by hand or spread on the surface of an inert material against which the animals rub themselves and thus transfer the product onto their skin. Lotions are distributed as low-volume amounts of liquid on the backs of animals, so that all or most of the liquid remains on the animals.
The compounds of formula (I) can be presented as ready-to-use compositions for use on plants, animals or surfaces, or in the form of compositions which need to be diluted before use, but both types of compositions contain a compound of formula (I) intimately mixed with one or more excipients or diluents. The excipients can be liquid, solid or gaseous, or can contain mixtures of such substances, and the compound of formula (I) can be present in a concentration of 99 to 0.025% w/v., according to whether the composition needs a stronger or weaker dilution. Dusting products, powders and granules contain the compound of formula (I) intimately mixed with a pulverulent solid inert excipient, for example suitable clays, kaolin, bentonite, attapulgite, adsorbent carbon black, talc, mica, chalk, gypsum, tricalcium phosphate, powdered cork, magnesium silicate, vegetable excipients, starch and diatomaceous earths. These solid compositions are in general prepared by impregnating the solid diluents with solutions of the compound of formula (I) in volatile solvents, by evaporating the solvents and, if appropriate, grinding of the products to obtain powders and, if desired, by granulating, compacting or encapsulating the products.
The sprays of a compound of formula (I) can contain a solution in an organic solvent (for example those mentioned above) or an emulsion in water (dipping or spraying), prepared on site from an emulsifiable concentrate (otherwise known as oil miscible with water), which can also be used for dipping. The concentrate preferably contains a mixture of the active ingredient, with or without organic solvent, and one or more emulsifiers. Solvents can be present in very variable quantities, but preferably in a quantity of 0 to 90% w/v of the composition, and can be chosen from kerosene, ketones, alcohols, xylene, aromatic naphtha, and other solvents known for use in compositions. The concentration of emulsifiers can be very variable, but is preferably in the range of 5 to 25% w/v, and the emulsifiers are advantageously non-ionic surfactants, in particular polyoxy-alkylenic esters of alkylphenols and polyoxyethylenic derivatives of hexitol anhydrides or anionic surfactants, in particular sodium laurylsulfate, fatty alcohol ethersulfates, the sodium and calcium salts of alkylarylsulfonates and alkylsulfo-succinates.
The cationic emulsifiers are in particular benzalkonium chloride and quaternary ammonium ethylsulfates.
The amphoteric emulsifiers are in particular carboxymethylated oleic imidazoline and alkyldimethyl-betaines.
Vaporization wicks normally contain a mixture of cotton and cellulose compressed into a pad, e.g. of approximately 32 mm by 22 mm by 3 mm, treated with, normally, up to 0.3 ml of a concentrate which contains the active ingredient in an organic solvent and optionally an anti-oxidant, a coloring agent and a perfume.
The insecticide may be vaporized by using a heat source, such as an electrically-powered device for heating the wicks.
The combustible solids normally contain sawdust and a binder mixed with the active ingredient and used in the form of molded strips (usually in coils). A coloring agent and a fungicide can also be added.
The wettable powders contain an inert solid excipient, one or more surfactants, and optionally stabilizers and/or anti-oxidants.
The emulsifiable concentrates contain emulsifying agents and often an organic solvent, such as kerosene, ketones, alcohols, xylenes, aromatic naphtha and other known solvents.
The wettable powders and emulsifiable concentrates normally contain 5 to 95% by weight of the active ingredient and are diluted, for example with water, before use.
The lacquers contain a solution of the active ingredient in an organic solvent, together with a resin and optionally a plastizer.
Dips can be prepared not only from emulsifiable concentrates, but also from wettable powders, dips based on soap and aqueous suspensions containing a compound of formula (I) intimately mixed with a dispersing agent and one or more surfactants.
The aqueous suspensions of a compound of formula (I) can include a suspension in water together with suspension agents, stabilizers or other agents. The suspensions or solutions can be applied as they are or in a form diluted in a known manner.
The ointments (or greases) can be prepared from vegetable oils, synthetic esters of fatty acids or lanolin, together with an inert base such as soft paraffin. A compound of formula (I) is preferably distributed uniformly throughout the mixture, in solution or in suspension. Ointments can also be obtained from emulsifiable concentrates by dilution of the latter with an ointment base.
The pastes and shampoos are also semi-solid compositions in which a compound of formula (I) can be present in uniform dispersion in a suitable base such as soft or liquid paraffin, or in a non-fat base with glycerol, a glue or a suitable soap. Since the ointments, shampoos and pastes are normally applied without any other dilution, they must contain the appropriate percentage of the compound of formula (I) required for the treatment.
Aerosol sprays can be prepared in the form of a simple solution of the active ingredient in the aerosol propellant and the co-solvent, such as a halogenated alkane and the above-mentioned solvents, respectively. The lotion compositions can be presented as a solution or a suspension of a compound of formula (I) in a liquid medium. A bird or mammalian host can also be protected against infestation by acarid ectoparasites by wearing a manufactured product in molded plastic of suitable form which is impregnated with a compound of formula (I). These manufactured products include collars, ear tags, bands, sheets and ribbons fixed in an adequate manner to the appropriate part of the body. Advantageously, the plastic material is a poly(vinyl chloride).
Therefore, a subject of the invention is in particular a composition containing:
a) a compound of formula (I) as defined previously,
b) inert excipients suitable for use as pesticides of said product of formula (I),
a composition containing:
a) a compound of formula (I) as defined previously,
b) inert excipients suitable for use in the veterinary field of said product of formula (I)
and a compound of formula (I) as defined previously, for the implementation of a treatment method for the human or animal body which comprises applying a pharmaceutically acceptable formulation of said compound to said body.
The compounds of formula (I) are also useful in the protection and the treatment of plant species, in which case an effective insecticide, acaricide, molluscide or nematocide quantity of the active ingredient is applied. The application rate will vary according to the chosen compound, the nature of the composition, the method of application, the type of plant, the density of plantation, the probable infestation, and other factors, but, in general, a suitable application rate for agricultural crops is in the range of 0.001 to 3 kg per hectare, and preferably between 0.01 and 1 kg per hectare. Typical compositions for agricultural use contain between 0.0001% and 50% of a compound of formula (I) and, advantageously, between 0.1 and 15% by weight of a compound of formula (I).
The concentration of the compound of formula (I) for an application on an animal, in premises or in outside areas varies according to the chosen compound, the interval between treatments, the nature of the composition and the probable infestation, but, in general the compound must be contained in the composition applied in a quantity of 0.001 to 20.0% w/v and preferably 0.01 to 10% w/w. The quantity of compound deposited on an animal varies according to the application method, the size of the animal, the concentration of the compound in the composition applied, the dilution factor of the composition and the nature of the composition, but is generally in the range of 0.0001% to 0.5% w/w, except for undiluted compositions, such as lotion compositions which are in general deposited at a concentration in the range of 0.1 to 20.0%, and preferably 0.1 to 10%. The quantity of compound to be applied on stored products is in general in the range of 0.1 to 20 ppm. Sprays can be applied in areas so as to obtain an initial average concentration of 0.001 to 1 mg of compound of formula (I) per m3 of treated area.
The ointments, greases, pastes and aerosols are usually applied at random, as described above and concentrations of 0.001 to 20% w/v of a compound of formula (I) in the compound applied can be used.
The compounds of formula (I) are particularly active against lipidoptera such as Spodoptera littoralis, Heliothis virescens, Plutella xylostella, against coleoptera such as Leptinotarsa decemlineata and Phaedon cochleariae. 
The compounds of formula (I) are thus useful for combating arthropods, for example insects and acaridae, in any environment in which they are harmful, for example in agriculture, in breeding, in public health and in domestic situations.
The harmful insects are in particular members of the orders of coleoptera (for example Anobium, Ceutorrhynchus, Rhynchophorus, Cosmopolites, Lissorhoptrus, Meligethes, Hypothenemus, Hylesinus, Acalymma, Lema, Psylliodes, Leptinotarsa, Gonocephalum, Agriotes, Dermolepida, Heteronychus, Phaedon, Tribolium, Sitophilus, Diabrotica, Anthonomus or Anthrenus spp.), lepidoptera (for example Ephestia, Mamestra, Earias, Pectinophora, Ostrinia, Trichoplusia, Pieris, Laphygma, Agrotis, Amathes, Wiseana, Tryporysa, Diatraea, Sparganothis, Cydia, Archips, Plutella, Chilo, Heliothis, Spodoptera littoralis, Helrotuis virescens, Spodoptera or Tineola spp.), diptera (for example Musca, Aedes, Anopheles, Culex, Glossina, Simulium, Stomoxys, Haematobia, Tabanus, Hydrotaea, Lucilia, Chrysomyia, Callitroga, Dermatobia, Gasterophilus, Hypoderma, Hylemyia, Atherigona, Chlorops, Phytomyza, Ceratitis, Liriomyza and Melophagus spp.), phthiraptera (Mallophaga, for example Damalina spp. and Anoplura, for example Linognathus and Haematopinus spp.), hemiptera (for example Aphis, Bemisia, Phorodon, Aeneolamia, Empoasca, Parkinsiella, Pyrilla, Aonidiella, Coccus, Pseudococcus, Helopeltis, Lygus, Dysdercus, Oxycarenus, Nezara, Aleyrodes, Triatoma, Psylla, Myzus, Megoura, Phylloxera, Adelges, Nilaparvata, Nephrotettix or Cimex spp.), orthoptera (for example Locusta, Gryllus, Schistocerca or Acheta spp.), dictyoptera (for example Blattella, Periplaneta or Blatta spp.), hymenoptera (for example Athalia, Cephus, Atta, Solenopsis or Monomorium spp.), isoptera (for example Odontotermes and Reticulitermes spp.), siphonaptera (for example Ctenocephalides or Pulex spp.), thysanura (for example Lepisma spp.), dermaptera (for example Forficula spp.), psocoptera (for example Peripsocus spp.) and thysanoptera (for example Thrips tabaci).
Harmful acaridae are in particular ticks, for example the members of the following genera: Boophilus, Ornithodorus, Rhipicephalus, Amblyomma, Hyalomma, Ixodes, Haemaphysalis, Dermacentor and Anocentor, and acaridae and mites such as Acarus, Tetranychus, Psoroptes, Notoednes, Sarcoptes, Psorergates, Chorioptes, Eutrombicula, Demodex, Panonychus, Bryobia, Eriophyes, Blaniulus, Polyphagotarsonemus, Scutigerella and Oniscus spp.
Nematodes which attack large plants and trees in agriculture, in forestry and in horticulture, either directly, or by spreading bacterial, viral, mycoplasmal or fungal diseases of plants, are in particular root node nematodes, such as Meloidogyne spp. (for example M. incognita); cyst nematodes, such as Globodera spp. (for example G. rostochiensis); Heterodera spp. (for example H. avenae); Radopholus spp. (for example R. similis); grassland nematodes, such as Pratylenchus spp. (for example P. pratensis); Belonolaimus spp. (for example B. gracilis); Tylenchulus spp. (for example T. semipenetrans); Rotylenchulus spp. (for example R. reniformis); Rotylenchus spp. (for example R. robustus); Helicotylenchus spp. (for example H. multicinctus); Hemicycliophora spp. (for example H. gracilis); Criconemoides spp. (for example C. similis); Trichodorus spp. (for example T. primitivus); tusk nematodes, such as Xiphinema spp. (for example X. diversicaudatum), Longidorus spp. (for example L. elongatus); Hoplolaimus spp. (for example H. coronatus); Aphelenchoides spp. (for example A. ritzemabosi, A. besseyi); and bulb nematodes, such as Ditylenchus spp. (for example D. dipsaci).
The compounds of the invention can be combined with one or more other active pesticides constituents (for example pyrethroids, carbamates and organophosphates) and/or with attractants, repellents, bactericides, fungicides, nematocides, anthelminthics and similar products. Furthermore, it has been observed that the activity of the compounds of the invention can be improved by the addition of a synergic or potentiating agent, for example a synergic agent of the class of oxidase inhibitors, such as piperonyl-butoxide, or propyl 2-propynylphenyl phosphonate, by the addition of a second compound of the invention or a pyrethroid pesticide. When an oxidase-inhibiting synergic agent is present in a composition of the invention, the ratio of the synergic agent to the compound of formula (I) is in the range of 25:1 to 1:25, for example approximately 10:1.
Stabilizers used to prevent any chemical decomposition of the compounds of the invention are in particular, for example, anti-oxidants (such as tocopherols, butylhydroxy-anisole and butylhydroxytoluene), vitamin C (ascorbic acid) and oxygen trapping agents (such as epichlorhydrin) similarly organic or mineral bases, for example trialkylamines, such as triethylamine, which can act as basic stabilisers and trapping agents.
The compounds of the present invention have increased pesticide properties and photostability and/or a reduced toxicity for mammals.
A subject of the invention is also a preparation process for the compounds of formula (I), wherein a compound of formula (II): 
in which a, b, c, d, X, Y, W, Q, Z, n and R retain their previous meaning and Dxe2x80x2 represents a hydroxy radical, a halogen atom, an alkoxy group containing up to 4 carbon atoms or a xe2x80x94P(O)(Oxcfx86)NHxcfx86 group in which xcfx86 represents a phenyl group, is subjected to the action of a compound of formula (III): 
in which R1 and R2 retain their previous meaning in order to obtain the corresponding compound of formula (I), which is modified, if desired, in order to obtain another product of formula (I).
The products of formula (I) thus obtained can be, if appropriate, separated into their optically active isomers.
The products of formula (II) are prepared, for example, according to processes described hereafter in the experimental part, starting, e.g., from products described by M. Elliott et al., Pest. Sce 1989, 26199 (called ref. 1 in the experimental part), or by L. A. Cornelius et al., Syn. Comm. 1994, 24 (10) 2777 (called hereafter ref. 2), or starting from products prepared according to methods indicated by these authors.
Separation of the isomers can be carried out according to methods known to a person skilled in the art for example by crystallization or by chromatography.
The amidification reaction is in general carried out at a temperature comprised between xe2x88x9225xc2x0 C. and 150xc2x0 C. in an anhydrous and aprotic solvent such as ether, dichloromethane, toluene or benzene.
Workup and purification can be carried out by routine methods well known to s.o. skilled in the art.
The compounds of formula (II) used as starting material are new and are in themselves a subject of the present invention.
The disclosures in French patent application No. 97 01 541 from which this application claims priority, and in the abstract accompanying this application are incorporated herein by reference.